Lufotrelvir

Lufotrelvir
Legal status
Legal status	US: Investigational drug ;
Identifiers
	IUPAC name [(3S)-3-[(2S)-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamido]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butoxy]phosphonic acid;
CAS Number	2468015-78-1;
PubChem CID	154699467;
DrugBank	DB16514;
UNII	XJ51YOB1SC;
KEGG	D12172;
ChEBI	CHEBI:173073;
Chemical and physical data
Formula	C24H33N4O9P
Molar mass	552.521 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)COP(=O)(O)O)NC(=O)C2=CC3=C(N2)C=CC=C3OC;
	InChI InChI=1S/C24H33N4O9P/c1-13(2)9-18(28-24(32)19-11-15-16(26-19)5-4-6-21(15)36-3)23(31)27-17(10-14-7-8-25-22(14)30)20(29)12-37-38(33,34)35/h4-6,11,13-14,17-18,26H,7-10,12H2,1-3H3,(H,25,30)(H,27,31)(H,28,32)(H2,33,34,35)/t14-,17-,18-/m0/s1; Key:FQKALOFOWPDTED-WBAXXEDZSA-N;

Lufotrelvir (PF-07304814) is an antiviral drug developed by Pfizer which acts as a 3CL protease inhibitor.^[1] It is a prodrug with the phosphate group being cleaved in vivo to yield the active agent PF-00835231.^[2] Lufotrelvir is in human clinical trials for the treatment of COVID-19, and shows good activity against COVID-19 including several variant strains, but unlike the related drug nirmatrelvir it is not orally active and must be administered by intravenous infusion, and so has been the less favoured candidate for clinical development overall.^[3]^[4]^[5]

References[]

^ Hoffman RL, Kania RS, Brothers MA, Davies JF, Ferre RA, Gajiwala KS, et al. (November 2020). "Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19". Journal of Medicinal Chemistry. 63 (21): 12725–12747. doi:10.1021/acs.jmedchem.0c01063. PMC 7571312. PMID 33054210.
^ Boras, Britton; Jones, Rhys M.; Anson, Brandon J.; Arenson, Dan; Aschenbrenner, Lisa; Bakowski, Malina A.; Beutler, Nathan; Binder, Joseph; Chen, Emily; Eng, Heather; Hammond, Holly (2021-10-18). "Preclinical characterization of an intravenous coronavirus 3CL protease inhibitor for the potential treatment of COVID19". Nature Communications. 12 (1): 6055. Bibcode:2021NatCo..12.6055B. doi:10.1038/s41467-021-26239-2. ISSN 2041-1723. PMC 8523698. PMID 34663813.
^ de Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, et al. (February 2021). "A comparative analysis of SARS-CoV-2 antivirals characterizes 3CL^pro inhibitor PF-00835231 as a potential new treatment for COVID-19". Journal of Virology. 95 (10). doi:10.1128/JVI.01819-20. PMC 8139662. PMID 33622961.
^ Baig MH, Sharma T, Ahmad I, Abohashrh M, Alam MM, Dong JJ (March 2021). "Is PF-00835231 a Pan-SARS-CoV-2 Mpro Inhibitor? A Comparative Study". Molecules. 26 (6): 1678. doi:10.3390/molecules26061678. PMC 8002701. PMID 33802860.
^ Vandyck K, Deval J (August 2021). "Considerations for the discovery and development of 3-chymotrypsin-like cysteine protease inhibitors targeting SARS-CoV-2 infection". Current Opinion in Virology. 49: 36–40. doi:10.1016/j.coviro.2021.04.006. PMC 8075814. PMID 34029993.

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[1] Hoffman RL, Kania RS, Brothers MA, Davies JF, Ferre RA, Gajiwala KS, et al. (November 2020). "Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19". Journal of Medicinal Chemistry. 63 (21): 12725–12747. doi:10.1021/acs.jmedchem.0c01063. PMC 7571312. PMID 33054210.

[2] Boras, Britton; Jones, Rhys M.; Anson, Brandon J.; Arenson, Dan; Aschenbrenner, Lisa; Bakowski, Malina A.; Beutler, Nathan; Binder, Joseph; Chen, Emily; Eng, Heather; Hammond, Holly (2021-10-18). "Preclinical characterization of an intravenous coronavirus 3CL protease inhibitor for the potential treatment of COVID19". Nature Communications. 12 (1): 6055. Bibcode:2021NatCo..12.6055B. doi:10.1038/s41467-021-26239-2. ISSN 2041-1723. PMC 8523698. PMID 34663813.

[3] Vries M, Mohamed AS, Prescott RA, Valero-Jimenez AM, Desvignes L, O'Connor R, et al. (February 2021). "A comparative analysis of SARS-CoV-2 antivirals characterizes 3CL^pro inhibitor PF-00835231 as a potential new treatment for COVID-19". Journal of Virology. 95 (10). doi:10.1128/JVI.01819-20. PMC 8139662. PMID 33622961.

[4] Baig MH, Sharma T, Ahmad I, Abohashrh M, Alam MM, Dong JJ (March 2021). "Is PF-00835231 a Pan-SARS-CoV-2 Mpro Inhibitor? A Comparative Study". Molecules. 26 (6): 1678. doi:10.3390/molecules26061678. PMC 8002701. PMID 33802860.

[5] Vandyck K, Deval J (August 2021). "Considerations for the discovery and development of 3-chymotrypsin-like cysteine protease inhibitors targeting SARS-CoV-2 infection". Current Opinion in Virology. 49: 36–40. doi:10.1016/j.coviro.2021.04.006. PMC 8075814. PMID 34029993.

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Legal status

Legal status	US: Investigational drug
Identifiers
IUPAC name [(3S)-3-[(2S)-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamido]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butoxy]phosphonic acid
CAS Number	2468015-78-1
PubChem CID	154699467
DrugBank	DB16514
UNII	XJ51YOB1SC
KEGG	D12172
ChEBI	CHEBI:173073
Chemical and physical data
Formula	C₂₄H₃₃N₄O₉P
Molar mass	552.521 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)COP(=O)(O)O)NC(=O)C2=CC3=C(N2)C=CC=C3OC
InChI InChI=1S/C24H33N4O9P/c1-13(2)9-18(28-24(32)19-11-15-16(26-19)5-4-6-21(15)36-3)23(31)27-17(10-14-7-8-25-22(14)30)20(29)12-37-38(33,34)35/h4-6,11,13-14,17-18,26H,7-10,12H2,1-3H3,(H,25,30)(H,27,31)(H,28,32)(H2,33,34,35)/t14-,17-,18-/m0/s1 Key:FQKALOFOWPDTED-WBAXXEDZSA-N

Lufotrelvir

See also[]

References[]